TW438780B - Quinazolone derivatives and a hair-growing agent and an agent for use on skin - Google Patents

Quinazolone derivatives and a hair-growing agent and an agent for use on skin Download PDF

Info

Publication number: TW438780B
Authority: TW; Taiwan
Prior art keywords: group; compound; reaction; acid; paper
Prior art date: 1997-08-21

Application number

TW087113765A

Other languages

English (en)

Chinese (zh)

Inventor

Koji Kobayashi

Hirotada Fukunishi

Tsunao Magara

Original Assignee

Shiseido Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-08-21

Filing date

1998-08-21

Publication date

2001-06-07

1998-08-21 Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd

2001-06-07 Application granted granted Critical

2001-06-07 Publication of TW438780B publication Critical patent/TW438780B/zh

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000003277 amino group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 12
OKDGPOCKHMGDQY-UHFFFAOYSA-N 3,4-dihydropyrrol-2-one Chemical class O=C1CCC=N1 OKDGPOCKHMGDQY-UHFFFAOYSA-N 0.000 claims description 8
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 6
150000007857 hydrazones Chemical class 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
235000001258 Cinchona calisaya Nutrition 0.000 claims 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
125000000623 heterocyclic group Chemical group 0.000 abstract description 9
125000005843 halogen group Chemical group 0.000 abstract description 7
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229940127557 pharmaceutical product Drugs 0.000 description 1
PXBGQFYGVFUKNE-UHFFFAOYSA-N phosphanium;acetate Chemical compound [PH4+].CC([O-])=O PXBGQFYGVFUKNE-UHFFFAOYSA-N 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
239000000419 plant extract Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
AHSYKBDQYRFAKE-UHFFFAOYSA-N pyridine;1,2-xylene Chemical compound C1=CC=NC=C1.CC1=CC=CC=C1C AHSYKBDQYRFAKE-UHFFFAOYSA-N 0.000 description 1
VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940092258 rosemary extract Drugs 0.000 description 1
235000020748 rosemary extract Nutrition 0.000 description 1
239000001233 rosmarinus officinalis l. extract Substances 0.000 description 1
229940119485 safflower extract Drugs 0.000 description 1
239000004248 saffron Substances 0.000 description 1
235000013974 saffron Nutrition 0.000 description 1
235000015067 sauces Nutrition 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
210000002374 sebum Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
229940063675 spermine Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
KRNGJNQVZMBTAF-UHFFFAOYSA-N tetradecane-1-sulfonyl chloride Chemical compound CCCCCCCCCCCCCCS(Cl)(=O)=O KRNGJNQVZMBTAF-UHFFFAOYSA-N 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
229960000716 tonics Drugs 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
229940117960 vanillin Drugs 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Birds (AREA)
Dermatology (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW087113765A 1997-08-21 1998-08-21 Quinazolone derivatives and a hair-growing agent and an agent for use on skin TW438780B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP24036297		1997-08-21

Publications (1)

Publication Number	Publication Date
TW438780B true TW438780B (en)	2001-06-07

Family

ID=17058372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW087113765A TW438780B (en)	1997-08-21	1998-08-21	Quinazolone derivatives and a hair-growing agent and an agent for use on skin

Country Status (7)

Country	Link
US (1)	US5972929A (fr)
EP (1)	EP0903344B1 (fr)
KR (1)	KR19990023754A (fr)
CN (1)	CN1218048A (fr)
AU (1)	AU735129B2 (fr)
DE (1)	DE69842109D1 (fr)
TW (1)	TW438780B (fr)

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CH689821A5 (it) *	1998-06-22	1999-12-15	Gecomwert Anstalt	Lozione tricologica ad uso topico.
WO2000029425A1 (fr) *	1998-11-13	2000-05-25	Kyowa Hakko Kogyo Co., Ltd.	Peptides actifs physiologiquement
US7671200B2 (en)	1999-10-27	2010-03-02	Cytokinetics, Inc.	Quinazolinone KSP inhibitors
US7230000B1 (en)	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
US6545004B1 (en)	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
WO2003043995A1 (fr)	2001-11-20	2003-05-30	Cytokinetics, Inc.	Procede de racemisation de quinazolinones chirales
JP2005529076A (ja)	2002-02-15	2005-09-29	サイトキネティクス・インコーポレーテッド	キナゾリノンの合成
RU2004135554A (ru)	2002-05-09	2006-01-20	Цитокинетикс, Инк. (Us)	Пиримидиноны, композиции на их основе и способы их использования
EP1553931A4 (fr)	2002-05-09	2006-08-30	Cytokinetics Inc	Composes, compositions et procedes
EP1513820A4 (fr)	2002-05-23	2006-09-13	Cytokinetics Inc	Composes, compositions et procedes
CA2489367A1 (fr)	2002-06-14	2003-12-24	Cytokinetics, Inc.	Composes, compositions et procedes
EP1537089A4 (fr)	2002-07-23	2008-04-16	Cytokinetics Inc	Composes, compositions et procedes
WO2004034972A2 (fr)	2002-09-30	2004-04-29	Cytokinetics, Inc.	Composes, compositions, et procedes
WO2005030131A2 (fr) *	2003-09-23	2005-04-07	Replidyne, Inc	Composes de bis-quinazoline pour le traitement des infections bacteriennes
EP1692112A4 (fr)	2003-12-08	2008-09-24	Cytokinetics Inc	Composes, compositions, et methodes associees
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EP2066289A4 (fr) *	2006-08-25	2013-11-27	Micellbio Co Ltd	Utilisations d'éléments terres rares pour le traitement capillaire
KR100769260B1 (ko) *	2006-08-25	2007-10-22	주식회사 태웅이엘에스	희토원소를 함유하는 모발 개선용 조성물
JP2010504974A (ja) *	2006-09-28	2010-02-18	フォリカ，インコーポレーテッド	新しい毛嚢を生成させ毛髪を成長させる方法、キット、及び組成物

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EP0293500A1 (fr) *	1987-06-01	1988-12-07	American Cyanamid Company	3-Hétéroalkyl-2,4-quinazoline-diones, 3-hétéroaryl-1,2,3-benzotriazin-4(3H)-ones, 3-hétéroarylalkyl-4-quinazolinone
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1998
- 1998-08-20 EP EP98115662A patent/EP0903344B1/fr not_active Expired - Lifetime
- 1998-08-20 DE DE69842109T patent/DE69842109D1/de not_active Expired - Lifetime
- 1998-08-20 US US09/137,148 patent/US5972929A/en not_active Expired - Lifetime
- 1998-08-21 TW TW087113765A patent/TW438780B/zh active
- 1998-08-21 KR KR1019980033871A patent/KR19990023754A/ko not_active Ceased
- 1998-08-21 AU AU80876/98A patent/AU735129B2/en not_active Ceased
- 1998-08-21 CN CN98120339A patent/CN1218048A/zh active Pending

Also Published As

Publication number	Publication date
AU735129B2 (en)	2001-06-28
CN1218048A (zh)	1999-06-02
US5972929A (en)	1999-10-26
EP0903344A1 (fr)	1999-03-24
EP0903344B1 (fr)	2011-01-26
KR19990023754A (ko)	1999-03-25
AU8087698A (en)	1999-03-04
DE69842109D1 (de)	2011-03-10

Legal Events

Date	Code	Title	Description
2001-10-11	GD4A	Issue of patent certificate for granted invention patent

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JPH0525106A (ja)	1993-02-02	カルボキシベタイン誘導体及びこれを含有する化粧料
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